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Towards the synthesis of a fluorinated diphosphine compound for the study of C-F activation

Jahangiri, Amita LU (2012) KEMR11 20121
Department of Chemistry
Abstract
The Wendt group at LU has recently developed a new class of sp3 pincer type ligands through
the selective C-H bond activation which introduced a rare example of PC(sp3)P pincer Pd(II)
complex.
In the present study, we aim to obtain insight into the selective cleavage of the sp3 C-F bond
by insertion of iridium metal. We are particularly interested in performing this reactivity on a
gem-diflouro, syn-diphosphine structure for studying sp3 C-F bond activation to generate an
entirely new class of coordination compounds.
Abstract
Popular Science Summary
The aim of this thesis is to develop a method for the selective cleavage of a carbon fluorine
bond with a transition metal. The main focus is directed towards the synthesis of a gemdifluoro,
syn-diphosphine compound XX. When treated with iridium the metal should bind to
the phosphines which keeps it close enough to the carbon fluorine bond to break it and form
what is known as a PC(F)P pincer type product like XX which would represent an entirely
new class of coordination compounds.
Two synthetic reaction pathways were examined for the synthesis of the gem-difluoro
compound XX. The first attempt was a three-step synthesis outgoing from a known
cyclization of an acetonedicarboxylate followed by a... (More)
Popular Science Summary
The aim of this thesis is to develop a method for the selective cleavage of a carbon fluorine
bond with a transition metal. The main focus is directed towards the synthesis of a gemdifluoro,
syn-diphosphine compound XX. When treated with iridium the metal should bind to
the phosphines which keeps it close enough to the carbon fluorine bond to break it and form
what is known as a PC(F)P pincer type product like XX which would represent an entirely
new class of coordination compounds.
Two synthetic reaction pathways were examined for the synthesis of the gem-difluoro
compound XX. The first attempt was a three-step synthesis outgoing from a known
cyclization of an acetonedicarboxylate followed by a fluorination reaction. The result of this
proposed synthetic pathway was not successful and leading to design another synthetic
reaction route which was a seven step reaction sequence where we selectively mask parts of
the molecule that can cause side reactions at various points. Unfortunately this route led to the
formation of a related vinyl fluoride compound rather than the desired XX.
In conclusion, the desired gem-difluoro compound XX for as not reached via the two
examined strategies and towards a molecular vehicle for the study of sp3 C-F activation
further investigations are required. (Less)
Please use this url to cite or link to this publication:
author
Jahangiri, Amita LU
supervisor
organization
course
KEMR11 20121
year
type
H2 - Master's Degree (Two Years)
subject
keywords
Organisk kemi
language
English
id
3516440
date added to LUP
2013-03-04 11:01:28
date last changed
2013-06-01 03:39:40
@misc{3516440,
  abstract     = {Popular Science Summary
The aim of this thesis is to develop a method for the selective cleavage of a carbon fluorine
bond with a transition metal. The main focus is directed towards the synthesis of a gemdifluoro,
syn-diphosphine compound XX. When treated with iridium the metal should bind to
the phosphines which keeps it close enough to the carbon fluorine bond to break it and form
what is known as a PC(F)P pincer type product like XX which would represent an entirely
new class of coordination compounds.
Two synthetic reaction pathways were examined for the synthesis of the gem-difluoro
compound XX. The first attempt was a three-step synthesis outgoing from a known
cyclization of an acetonedicarboxylate followed by a fluorination reaction. The result of this
proposed synthetic pathway was not successful and leading to design another synthetic
reaction route which was a seven step reaction sequence where we selectively mask parts of
the molecule that can cause side reactions at various points. Unfortunately this route led to the
formation of a related vinyl fluoride compound rather than the desired XX.
In conclusion, the desired gem-difluoro compound XX for as not reached via the two
examined strategies and towards a molecular vehicle for the study of sp3 C-F activation
further investigations are required.},
  author       = {Jahangiri, Amita},
  keyword      = {Organisk kemi},
  language     = {eng},
  note         = {Student Paper},
  title        = {Towards the synthesis of a fluorinated diphosphine compound for the study of C-F activation},
  year         = {2012},
}